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Synlett
Volumn , Issue 5, 2009, Pages 0759-0762
Synthesis of ether-linkage-based cyclic glycerophospholipid carrying methylene moiety that improves membrane fluidity
Author keywords

Cyclic lipid; Ether lipid; FRAP; Lipids; Macrocycles; Phospholipid
Indexed keywords

EID: 62349118196     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087935     Document Type: Article
Times cited : (1)
References (24)
  • 18
    • 62349136361 scopus 로고    scopus 로고
    • +].
    • +].
  • 19
    • 62349087032 scopus 로고    scopus 로고
    • +].
    • +].
  • 20
    • 62349138145 scopus 로고    scopus 로고
    • +].
    • +].
  • 21
    • 62349115122 scopus 로고    scopus 로고
    • Procedure for the Preparation of 13 To a solution of Cu(OAc) 2 (314 mg, 1.73 mmol) in refluxing pyridine (100 mL, a solution of 12 (257 mg, 0.173 mmol) in pyridine (10 mL) was added dropwise with a syringe pump over 5.5 h. The solution gradually turned from blue to dark green. After completion of the addition the solution was heated at the same temperature for 1 h. The mixture was cooled to r.t. and evaporated to give a residue, which was purified on a silica gel column chromatography eluted with hexane-EtOAc (10:1) to give 13 as a yellow oil; yield 157 mg (61, 1H NMR (400 MHz, CDCl3, δ, 1.28 (24 H, br s, 1.39 (8 H, br m, 1.51-1.57 (16 H, br m, 1.96-2.01 (16 H, m, 2.28 (br s, 8 H, 3.13-3.20 (4 H, br m, 3.39 (4 H, br t, J, 6.9 Hz, 3.45-3.58 (10 H, m, 4.68 (8 H, br s, 7.20 (6 H, t, J, 7.1 Hz, 7.27 (12 H, t, J, 7.3 Hz, 7.45 (12 H, d, J, 7.8 Hz, ESI-MS TOF, m/z, 1505 [M
    • +].
  • 22
    • 62349116379 scopus 로고    scopus 로고
    • The sequence from 7 and glycerol moiety to 12 was altered from the one we previously reported for preparing a straight-chain analogue 1.10,11 At the step of the connection of chain moiety and protected glycerol in the previous study, we used 1-trityl-3-p-methoxybenzoyl-sn-glycerol, which was prepared by starting from 1,2-isopropylidene-sn-glycerol in three steps. Through this modification, several protection-deprotection steps could be omitted. The order in which the chains was introduced into the glycerol moiety was also changed. This change would cause an increase in the steric hindrance around the secondary hydroxy groups during the Williamson reaction sequence; however, the reaction proceeded without difficulties even though the yield of 12 was somewhat lower
    • 10,11 At the step of the connection of chain moiety and protected glycerol in the previous study, we used 1-trityl-3-p-methoxybenzoyl-sn-glycerol, which was prepared by starting from 1,2-isopropylidene-sn-glycerol in three steps. Through this modification, several protection-deprotection steps could be omitted. The order in which the chains was introduced into the glycerol moiety was also changed. This change would cause an increase in the steric hindrance around the secondary hydroxy groups during the Williamson reaction sequence; however, the reaction proceeded without difficulties even though the yield of 12 was somewhat lower.
  • 23
    • 62349107329 scopus 로고    scopus 로고
    • +].
    • +].

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.